52670-38-9

Basic information

• Product Name: 2-ETHYNYLANILINE 98
• Synonyms: 2-ETHYNYLANILINE 98;2-Ethynyl aniline (2-aminophenylacetylene);Benzenamine, 2-ethynyl- (9CI);2-Ethynylaniline;2-Ethynyl-phenylaMine;2-Ethynyl-benzenaMine;2-Ethynylaniline 98%;Benzenamine, 2-ethynyl-
• CAS NO: 52670-38-9
• Molecular Formula: C₈H₇N
• Molecular Weight: 117.14788
• Product Categories: Alkynes;Organic Building Blocks;Terminal
• Mol File: 52670-38-9.mol

Chemical Properties

• Boiling Point: 229-230 °C(lit.)
• Flash Point: 209 °F
• Appearance: /
• Density: 1.030 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.109mmHg at 25°C
• Refractive Index: n20/D 1.6200(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1?+-.0.10(Predicted)
• CAS DataBase Reference: 2-ETHYNYLANILINE 98(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ETHYNYLANILINE 98(52670-38-9)
• EPA Substance Registry System: 2-ETHYNYLANILINE 98(52670-38-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 52670-38-9(Hazardous Substances Data)

Usage

Uses

Used in Dye and Pigment Production:
2-Ethynylaniline 98 is used as an intermediate in the production of various dyes and pigments, contributing to the coloration and stability of these products in different industries.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-Ethynylaniline 98 serves as a building block for the synthesis of various pharmaceuticals, playing a crucial role in the development of new drugs and therapeutic agents.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical sector, 2-Ethynylaniline 98 is utilized as a building block for the synthesis of agrochemicals, aiding in the creation of products that enhance crop protection and yield.
Used in Organic Synthesis:
As a versatile reagent in organic synthesis, 2-Ethynylaniline 98 is used to undergo various chemical reactions, forming different derivatives for a wide range of applications across multiple industries.

InChI:InChI=1/C8H7N/c1-2-7-5-3-4-6-8(7)9/h1,3-6H,9H2

Upstream product

• 615-43-0 2-iodophenylamine 
• 143321-89-5 2,2,2-trifluoro-N-(2-iodophenyl)acetamide 
• 74-86-2 acetylene 
• 316795-01-4 2-(trimethylsilylethynyl)trifluoroacetanilide 
• 167558-54-5 2-(2,2-dibromo-vinyl)-phenylamine 
• 1066-54-2 trimethylsilylacetylene 
• 112671-41-7 N-{2-[(trimethylsilanyl)ethynyl]phenyl}benzamide 
• 112671-40-6 2-(trimethylsilylethynyl)formanilide 
• 110598-59-9 N-acetyl-2-<(trimethylsilyl)ethynyl>aniline 
• 79092-33-4 C₈H₄KLi 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 67177-79-1 phenylnitroacetylene 
• 16433-96-8 2-ethynyl-1-nitrobenzene 
• 614-76-6 N-acetyl-2-bromoaniline 

Downstream Products

• 186959-31-9 3,5-Bis-methylsulfanyl-[1,2,4]triazine-6-carboxylic acid (2-ethynyl-phenyl)-amide 
• 371153-70-7 2-benzyloxycarbonylaminophenylacetylene 
• 474335-72-3 (Z)-methyl N-(2-ethynylphenyl)acetimidate 
• 6637-33-8 2-(2'-aminophenyl)-4-methylquinoline 
• 852619-15-9 2-({2-[(trimethylsilyl)ethynyl]phenyl}ethynyl)aniline 
• 1023306-51-5 2-(6-trimethylsilyl-3(Z)-hexen-1,5-diynyl)aniline 
• 881038-82-0 o-(but-3-en-1-ynyl)aniline 
• 7461-34-9 N-benzyl-p-chlorobenzamide 
• 1006728-02-4 4-bromo-N-(2-ethynylphenyl)benzamide 
• 57707-20-7 4-chloro-N-cyclohexylbenzamide 
• 31661-58-2 2-[4-(2-aminophenyl)-1,3-butadienyl]phenylamine 
• 221910-19-6 2-(4-chlorophenylethynyl)phenylamine 

Relevant articles and documents

Metal-free cascade boron–heteroatom addition and alkylation with diazo compounds

Transition metal-catalyzed carbene transfer reaction is one of the most notable advances for C?C bond formation reactionsduring the past decade, which has been widely employed in the preparation of C3-substituted indoles. Here, we described an efficient e

Gold-Catalyzed Synthesis of π-Extended Carbazole-Based Systems and their Application as Organic Semiconductors

Herein we describe a gold-catalyzed bidirectional synthesis of N-heteropolycyclic compounds bearing carbazole moieties – namely π-extended benzodicarbazoles and π-extended indolocarbazoles. Overall, four previously unknown core structures were synthesized. This approach is convergent, modular and the gold-catalyzed key step comprises of a cascade reaction starting from stable di-azido compounds. The obtained molecules were fully characterized and their optical and electronic properties as well as their performance in organic thin-film transistors generated by vacuum deposition were studied. Charge-carrier mobilities of up to 0.3 cm2/Vs were measured. (Figure presented.).

New indolo[1,2-c]quinazolines for single-crystal field-effect transistor: A united experimental and theoretical studies

Here, we account the synthesis and characterization of a series of symmetrical fused heterocyclic aromatic hydrocarbons (HAHs) with an indolo[1,2-c]quinazoline (IQ) as the core moiety. All the new HAHs IQ series were systematically investigated by using various spectroscopic methods. Furthermore, their photo-physical properties were supported by density functional theory (DFT) and time-dependent density functional theory (TDDFT) studies to support the experimental findings. The tetramethyl-substituted indolo[1,2-c]quinazoline (TMIQ) compound is shown to exhibit the shifted type of π–π stacking interactions, which render this series as a new semiconducting material. Single-crystal-based field-effect transistor devices of TMIQ exhibited efficient charge transport behavior, giving a p-channel field-effect mobility of 0.25 cm2?V?1?s?1 with an on/off ratio of 5 × 105.

Metal-Free and syn-Selective Hydrohalogenation of Alkynes through a Pseudo-Intramolecular Process

A new metal-free hydrohalogenation method for alkynes has been developed, which proceeds through a pseudo-intramolecular process. In this reaction, ethynylaniline serves as a substrate to quantitatively form an anilinium salt upon treatment with hydrochloric acid. The spatial proximity facilitates the efficient electrophilic addition of HCl to the ethynyl group in syn-mode, affording the corresponding chloroalkene without overaddition. This protocol was applied to HBr and HI, and the corresponding bromo- and iodoalkenes were obtained, respectively. The obtained chloroalkene was converted to tri-substituted alkenes possessing different aryl/alkynyl groups through Pd-catalyzed cross-coupling reactions.

Optimization of 4,6-Disubstituted Pyrido[3,2-d]pyrimidines as Dual MNK/PIM Inhibitors to Inhibit Leukemia Cell Growth

Mitogen-activated protein kinase-interacting kinases (MNKs) and provirus integration in maloney murine leukemia virus kinases (PIMs) are downstream enzymes of cell proliferation signaling pathways associated with the resistance of tyrosine kinase inhibitors. MNKs and PIMs have complementary effects to regulate cap-dependent translation of oncoproteins. Dual inhibitors of MNKs and PIMs have not been developed. We developed a novel 4,6-disubstituted pyrido[3,2-d]pyrimidine compound 21o with selective inhibition of MNKs and PIMs. The IC50’s of 21o to inhibit MNK1 and MNK2 are 1 and 7 nM and those to inhibit PIM1, PIM2, and PIM3 are 43, 232, and 774 nM, respectively. 21o inhibits the growth of myeloid leukemia K562 and MOLM-13 cells with GI50’s of 2.1 and 1.2 μM, respectively. 21o decreases the levels ofp-eIF4E andp-4EBP1, the downstream products of MNKs and PIMs, as well as cap-dependent proteins c-myc, cyclin D1, and Mcl-1. 21o inhibits the growth of MOLM-13 cell xenografts without causing evident toxicity. 21o represents an innovative dual MNK/PIM inhibitor with a good pharmacokinetic profile.

New Indolo[3,2-b]indole based small organic molecules for Organic Thin Film Transistors (OTFTs): A combined experimental and DFT Study

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Sequential Sonogashira/intramolecular aminopalladation/cross-coupling ofortho-ethynyl-anilines catalyzed by a single palladium source: rapid access to 2,3-diarylindoles

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Copper-Catalyzed Trifluoromethylation/Cyclization of Alkynes for Synthesis of Dioxodibenzothiazepines

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